1,1'-Carbonyldiimidazole → N-Methoxy-N-methylpyrimidine-5-carboxamide

HRID 627497Notes

Reaction equation

HRID 627497 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[N:13]1[CH:18]=[C:17]([C:19]([OH:21])=O)[CH:16]=[N:15][CH:14]=1.Cl.[CH3:23][NH:24][O:25][CH3:26]>C(Cl)Cl.[NH4+].[Cl-].O>[CH3:26][O:25][N:24]([CH3:23])[C:19]([C:17]1[CH:16]=[N:15][CH:14]=[N:13][CH:18]=1)=[O:21]

Participants

7

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 78346Pyrimidine-5-carboxylic acidHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 66575045N-Methoxy-N-methylpyrimidine-5-carboxamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

1,1′-carbonyldiimidazole (1.23 g, 7.57 mmol) was added to a suspension of pyrimidine-5-carboxylic acid (783 mg, 6.31 mmol) in DCM (20 mL) and the mixture was stirred at room temperature for 15 min before addition of N,O-dimethylhydroxylamine hydrochloride (739 mg, 7.57 mmol). The mixture was stirred at room temperature for 5 d, then was diluted with saturated aqueous NH4Cl and water and extracted with DCM. The organic phase was washed with water, and the aqueous phases were back-extracted with DCM. The organic phase was dried (Na2SO4), filtered, and concentrated, affording the crude title compound as a light yellow oil which was used without further purification in the next reaction.

Workup

  1. extractionextracted with DCM
  2. washThe organic phase was washed with water
  3. extractionthe aqueous phases were back-extracted with DCM
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-342d1264d4624837979f120d69c22553
Source dataset
uspto-grants-2016_04
Patent number
US09309222B2

Reaction notes

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